Highly enantioselective direct Mannich reaction of seven-membered cyclic imines dibenzo[b,f][1,4]oxazepines with acetone via organocatalysis

doi:10.1016/S1872-2067(14)60225-4

Abstract

Abstract:

Various substituted dibenzo[b,f][1,4]oxazepines as seven-membered cyclic imines underwent a highly enantioselective direct Mannich reaction with acetone when catalyzed by proline. These reactions gave a range of optically active β-carbonyl seven-membered N-heterocycles with excellent enantioselectivity (93%-98% ee). With 2-butanone as a Mannich donor, the single regioselective product was obtained with 96%-97% ee. The absolute configuration of the product was assigned to be R by X-ray single crystal analysis of its derivative.

Key words: Acetone, Asymmetric catalysis, Seven-membered cyclic imine, Mannich reaction, Organocatalysis

You-Qing Wang, Yuan-Yuan Ren. Highly enantioselective direct Mannich reaction of seven-membered cyclic imines dibenzo[b,f][1,4]oxazepines with acetone via organocatalysis[J]. Chinese Journal of Catalysis, 2015, 36(1): 93-99.

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URL: https://www.cjcatal.com/EN/10.1016/S1872-2067(14)60225-4

https://www.cjcatal.com/EN/Y2015/V36/I1/93

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